Crossing the Opposite Side
by windearth
Summary: Mafia AU. The dull life of Detective Castiel Novak is about to change when a persistent mafia prince enter his life. Fluff!
1. Chapter 1

Hi again! It's my third fic for SPN fandom!

If it wasn't because my mother dragged my into a place with no internet connection and left me waiting alone for two hours there today, maybe I wouldn't type this fic yet, due to my laziness. With only iPhone in my hand and most of the puzzle games had already been completed and no way to disturb my friends, I decided to finally use the text editor application that I have downloaded months ago for the first time to type this fic, LOL.

I apologize in advance for any mistakes that you find, I will return later to re-check this fic after my eyes get enough rest. XD

Soo, please bear with me and enjoy my newest fic!

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><p><strong>Crossing the Opposite Side<strong>

**Chapter I  
><strong>

Castiel Novak was a homicide detective worked for New York Police Department, a first-class investigator who had gained a reputation by solving 53 cases since he joined the rank three years ago. Investigation was his specialization, thus making him one of the most trusted detectives in the department.

His good reputation was what had landed him in hard cases most of the times. Some of the cases were even having mafia involvement somehow, whether it was a murder or attack of a mafia henchman, or the otherwise. He was quite familiar with almost all of the mafia families in New York because of that.

There was a high pile of files of the mafia families in the dark haired detective's office, gathered by his agents since his first case that involved a mafia organization two years ago. He had memorized all the family members and the important henchmen, along with their positions, like an obsessed fan girl who had memorized all the names of the stars in her favorite movies.

From all the mafia families that he had investigated, there was one that suspiciously clears of any charge for over ten years, which was a weird thing for underworld organization who dealt mostly with illegal businesses. Although it was doubtlessly suspicious, the Winchester family was basically untouched by police as long as they weren't committing any crime. Unknown to other people in the precinct, he continued his investigation in discreet, reviewing the Winchester files that had been gathered by his agents whenever he had time between his caseload.

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><p>It was just Castiel's poor luck, that when his department received a call from a local bar at 10.40 p.m., informing about a bloody fight between two customers, he was the only detective from homicide department that was still stuck in the precinct, reviewing his latest case alone in the office.<p>

By the time he arrived at the location, the police were in the middle of securing the place to prevent the valuable witnesses from leaving. One of the poor bastards who were involved in the fight had already been taken to the hospital to attend his wounds, while the other one with minor injury were sitting in one of the bar stools with his back facing the detective, answering questions from a police officer. The bar owner and several waitresses had stood behind the bar, listening to them.

"Listen, dude! How many times do I have to explain this? I have told you everything that happened!" the blond haired man in business suit, their suspect, growled impatiently.

Sighing, Castiel decided to step in quickly before the seemingly hot-headed man starting another fight. "Thank you, Sir. I will take care of this from here," he told the police officer.

The officer quickly saluted him and stepped back, while the fuming man slowly turned toward him. Castiel's eyes widened in shock when he finally saw the blond man's face.

In front of him sat a man whose face had been familiar to him. A man whose face was on several surveillance photos and videos gathered by his agents, along with the other members of a mafia family. The man in front of him was none other than Dean Winchester, the mafia prince from Winchester family.

The blond haired stared back at Castiel in confusion for a split second, before quirking his lips up in an amused smile. "See something you like?" he teased the speechless detective.

Castiel glared at him, quickly composing himself and flashed out his badge. "I'm Detective Castiel Novak, from New York Police Department," he introduced himself coldly, deciding to ignore the other man's remark completely. "I'm here to ask you questions regarding the fight."

The blond haired man grinned at him. "Well, just ask then. I'll answer all of your questions as best as I can."

About half an hour later, Castiel concluded that the answers from the suspect were matching the explanation from the witnesses. The fight started because the mafia prince stepped in when the other suspect, in a drunken state, advancing on a poor waitress. All the people in the bar stood for him, telling the police to release him because he had done the right thing. Not finding any evidence to convict him, the mafia prince was freed of charge.

Once he had been informed that he was free to go, the mafia prince grinned smugly at the police officer who had arrested him earlier, before walking towards the detective.

"So, Cas," the mafia prince called him in such familiarity that made the smaller man frowned at him.

"Castiel," the detective corrected him firmly.

The blond haired man just grinned at him. "Castiel is mouthful," he commented nonchalantly, annoying the detective further. "By the way, Cas, I just realized that you didn't ask for my name yet."

The dark haired man raised an eyebrow, eyeing the proffered hand. He then returned the gesture slowly, letting the other man grabbed his hand for a handshake.

Smiling charmingly, the taller man introduced himself. "My name is Dean-"

"I know your name," Castiel cut him coldly, pulling out his hand from the other man's grasp. "Your name is Dean Winchester."

Ignoring the shocked expression on Dean's face, the detective turned and walked away from the blond haired man, his trench coat swirling behind him.

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><p>The coffee shop near NYPD headquarter was full that afternoon. Castiel regretted coming there as soon as he saw the long queue of people waiting for their turn to order at the cashier. He just contemplated to go back to office and told Gabriel, his detective partner, to go buy his coffee himself, when someone called his name. Loudly.<p>

Caught by surprise, he quickly turned around and saw the mafia prince who he had just met a week ago, sitting on one of the two-person tables in the corner. The blond haired man grinned at him, gesturing for the detective to sit on the chair across from him. The dark haired man sighed deeply, before walking towards him.

"May I help you?" Castiel asked in neutral tone, hiding his suspicion and wariness well enough. After disclosing the fact that he knew the about the other man on their meeting last week, the detective realized that he had made a grave mistake. The mafia family now knew that he had investigated them. He had prepared himself for the day when the Winchester would confront him; he just didn't expect it to be this soon.

Dean just eyed him amusedly. "Come on, Cas. Don't be so formal. Sit, I know you are tired after working a whole day."

Castiel pulled the empty chair then sat stiffly, eyeing the the other man back all the while. "So you have followed me all this time?"

The other man had the nerve to look confused. "Following you? No!" he replied quickly. "I just thought that since this coffee shop is near your base, I will be able to meet you here." Chuckling slightly, he continued, "It took longer time than I thought. I have started to think that maybe I should just wait for you in front of the precinct."

Castiel glared at him, starting to get impatient. "What do you want, Winchester?" he asked curtly. "Just get to the point. I don't have enough time for your game."

The blond haired man seemed taked aback by his hostility. "Whoa there. Relax, Cas!" he raised both of his hands in front of him in an attempt to calm the detective down. "I just want to know about you. Is it wrong?"

The dark haired man really wanted to answer _yes_, but decided against it. Instead, he intensified his glare and asked, "Oh? So what is it that you want to know about me?"

Dean seemed to be satisfied by his reply. He suddenly leaned forward, smiling in a way that made the detective started to feel uncomfortable. "Well, for starter, just call me Dean." When there was no reply from Castiel, the blond haired man continued. "Let's see. How about you tell me your favorite activity on your free times first?"

"It's none of your business."

"Your favorite hang out places?"

"It's none of your business."

The blond haired man didn't give up easily. "Your phone number?"

"What makes you think I would give my phone number to you?" Castiel retorted, deciding that he had enough.

Before Dean could answer him, his phone rang. Castiel quickly pulled his cell phone out from his trench coat pocket then looked at the caller name, before accepting the call. "Yes, Gabriel?"

"_Caaassyyy, where is my coffee? I barely able to open my eyes now!" _the voice from the other end of the receiver whined, making the dark haired detective rolled his eyes. _"By the way, Ash told me that he has gotten the information that you want. You better come back quickly!"_

Castiel contemplated to tell his partner about Dean Winchester, but after one glance at the blond haired man who had been staring at him intently, he decided that it wasn't a wise thing to do at this time. "Fine. Please tell Ash that I will be there shortly," he answered quickly, then ended the call before Gabriel could whine further.

"Call from work?" Dean asked him once he had pocketed his cell phone again.

"Yes," Castiel replied shortly, looking at the queue that had only three people left now. "If you don't have anything important to say, I will go order my coffee now," he told the mafia heir before standing up and going to join the queue.

Dean stood up from his chair as well and followed him from behind, much to the detective confusion. When the detective turned his head around to look at him questioningly, the blond haired man just smiled innocently. "What? I want to order coffee too."

The dark haired man knew better than to confront the mafia heir when they were standing in the queue. Slightly peeved, he turned to look ahead again, deciding to say nothing.

When it was Castiel's turn to order, he told the cashier quickly. "Two black coffees."

"Make it three," Dean piped up, stepping beside him and handing the money for three black coffees to the cashier.

Castiel stared at him in surprise. "Why are you paying for my order?"

The mafia prince just shrugged. "Just think of this as my token of apology for monopolizing your time and making you late to come back to your work."

"You don't have to do this, Mr. Winchester."

"Dean," the other man corrected him. "And Cas, it's not a big deal, okay?"

Before the detective could speak again, the cashier informed them. "Your order is ready, Sirs."

Sighing, Castiel decided to let the matter go. He muttered "Thank you" to Dean and took his order from the counter, one cup on each hand.

The blond haired man grinned widely at him and replied "You're welcome" before taking his own coffee and then following the detective walked out of the coffee shop.

Once they were outside, Dean called him, "Cas, wait!"

The dark haired man stopped and turned to face him. "Yes, Dean?" he asked impatiently, only to yelp a second later when the taller man suddenly crowded his space and slipped his free hand into the detective's trench coat pocket. He blushed furiously when the other man's hand_ accidentally_ touched his thigh.

When Dean stepped back, Castiel could see that his cell phone was on his hand. "What do you think you are doing? Give me back my cell phone!"

"Give me a moment, Cas," the blond haired man replied nonchalantly.

With both of his hands were occupied, the detective could only stare in horror when Dean pressed some numbers on his cell phone. "W-what are you doing?" His question was answered a moment later, when a ringtone suddenly played from inside of the other man's pocket.

Grinning victoriously, Dean pulled out his own cell phone and then flashed the screen to the dark haired man. "Got your number!" he told him smugly, before stepping forward to return the detective's cell phone back into his pocket.

Castiel stared at him with dumbfounded look on his face.

"I will call you soon, Cas!" The mafia prince winked at him and then walked away, leaving the bewildered detective behind.

_**To Be Continued**_

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><p>What do you think? Like this? Or dislike this? XD<p>

This fic would be short, maybe two more chapters. I promise that I at least would try to finish this one before even thinking to succumb to laziness once again, ahahah.

I really want to say that review will make the next chapter come sooner, but I know that it's not true. I couldn't promise a fast update anymore, sadly.

So I just want to say that review will motivate me to keep writing! That's what I can promise you!


	2. Chapter 2

Lots of thanks to all of you lovely readers who had reviewed the last chapter. The number of reviews that I got was really a surprise for me. I'm so glad to know that I have so many readers who like this fic, it's really a boost for my volatile writing spirit XD Thanks also to all of you who put this fic on story alert and also on favorite. Last time I checked the number I was pretty amazed, really.

To anon reviewer who mentioned about Dean's having brown hair, I will admit that at first I was also sure Dean's hair was brown. My belief was changed after I read SPN Wiki, in which it stated that Dean's hair is dirty blond. I googled that after I read your comment, and saw some debates over whether Dean's hair is dirty blond or light brown. But since I already mentioned that Dean's blond in all of my fic, I will stick to that till the end XD

Without further ado, please enjoy the second chapter!

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><p><strong>Crossing the Opposite Side<strong>

**Chapter II  
><strong>

Gabriel was the closest friend Castiel ever had, and the best partner he could ever hope for.

Since both of them were put on the same team together, they quickly became best friends despite their different personalities. It wasn't long until the older detective started to treat him like a little brother who he never had, with all the merciless teasing and the brotherly affection. Castiel was surely appreciating Gabriel's attention for him, thinking of the blond haired man as a brother too. The problem was, his attention was bordering on over-protectiveness.

That was why Castiel didn't tell his partner about Dean Winchester yet, despite his previous idea when he was faced with the mafia heir for the second time in that coffee shop. He didn't want to make him worry, not when there was a case that needed his undivided attention. He didn't dare to imagine how the blond haired detective would react when he know about his encounter with the heir of the Winchester family.

It was a hectic week for both Castiel and Gabriel. A case that had been investigated by their team for almost one month was finally come to an end. It was decidedly one of the most unique cases that he had ever handled, though not the hardest. The serial killer, a psycho man at his late thirtieth, at first was succesfully fooling them into believe that it was a random murder. It wasn't until last week that they started to see the pattern. After that, catching the killer was no longer a big problem. They ambushed him on his way to the seventh victim's house. In the end, the victim was safe, and the killer was caught.

In the rush of everything that happened in that week, Dean Winchester was put on the back of his mind, buried under the stress and fatique from his work.

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><p>The promised call came later that week, when Castiel had almost forgotten about it.<p>

Both he and Gabriel were in the middle of a meeting with their superiors, giving their report about the case, when Dean called him for the first time. The dark haired detective quickly excused himself from the meeting room upon reading the caller name and stormed out from there, ignoring the questioning looks from the people inside the room.

As soon as the door was closed, Castiel answered the call. "Detective Castiel Novak from New York Police Department. What can I do for you?" he asked coldly.

_"Hey, Cas. Sorry it took me one week to call you. I just back from Las Vegas today,"_the voice from the other end of the receiver explained.

The dark haired man blinked in bemusement, and then scoffed, "Do you think I'm waiting for your call?" He couldn't help but state that, because that was the truth. He had almost forgotten about Dean's promise to call him.

There was an amused chuckle. _"Cas, stop acting so cold towards me. You hurt my feelings here."_

Castiel glared weakly at the wall in front of him, before closing his eyes and slowly massaging his temple. "Look, Dean. I'm in the middle of a meeting now. If you don't have anything important to tell me, I will end the call now."

_"I just want to know the answer of my questions, you know?"_ Dean told him in somewhat playful tone.

"What?" the detective asked impatiently, feeling a headache started to form.

_"My questions from last week? I asked you about your favorite activities and favorite hang out places. You didn't answer those, remember?"_

"..."

_"Cas? Do you think I will use that information against you? Come on, I'm a good guy!"_

Castiel rolled his eyes, and then sighed in irritation. "I don't have time for this, Dean."

There was a short pause before Dean replied, _"Too bad."_ His voice sounded genuinely disappointed. Well, as if he cared. _"Just...call me back later when you're free, 'kay?"_

Castiel wordlessly ended the call.

Three days and seven phone calls later, the detective started to believe that the mafia prince was gaining satisfaction by messing with him. He rejected the eighth call as soon as he read the caller name, and did the same for the ninth call that came later in the afternoon.

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><p>The precinct was almost empty that night, safe for the night shift officers and several workers who still staying behind to finish whatever their jobs were. Castiel was just walking towards his car that parked not too far from the building, when someone called him from behind.<p>

"Hi, Cas."

Surprised, the detective turned around abruptly, right hand automatically reaching for his gun holster. His movement was put to a halt when he saw the man who had called him. "D-Dean?" he stuttered, eyes widening in disbelief. "What are you doing here?"

The taller man grinned mischiefully and strutted confidently towards him, before answering, "You've been ignoring my phone call lately. What else can I do to keep in touch with you besides meeting you in person?"

Castiel gave him an annoyed, suffering look, before sighing exasperatedly. "What do you want?"

Dean just kept walking closer towards him, grinning all the while. "Cold as always," he commented playfully once he had stopped about three feet in front of him. "Can't you be nice at least once to me, Cas?"

Castiel tilted his head to a side. "I don't see the reason of why I should be nice to you." There was an unspoken statement that followed his sentence, _because I'm a cop and you're a mafia member_.

Dean snorted at him, before leaning in as if want to say something that only meant for his ears. "I know a good bar that serve the best drink in this city, let's go there," Dean said in a suggestive tone that caused an embarrassed blush starting to creep on the detective's cheek. "I'll help you loosen up."

Taking a step back to gain some of his personal space back, Castiel scoffed at him, "Thank you for your offer, but no."

His reply seemed to amuse Dean further. "Cas, has anyone told you how tight you are?" he asked, a tint of mirth in his voice.

The dark haired detective threw a glare at him. "Almost all of my family. And co-workers," he replied in a bland tone.

Dean laughed out loud at that, which only served to irritate the dark haired man further.

"Good night, Dean," Castiel said curtly and then turned to leave the other man.

"Wait!" Dean called him, catching the smaller man off guard when he suddenly lurched forward and grabbed the smaller man's wrist to stop him from leaving. "Sorry! I'm sorry!" he said between laugh. "I'll stop laughing now!"

Castiel glared at him all the while. "Are you done yet? Release me now," he said after the other man's laughter died down, tugging at his hand that was still clutched on a firm grip.

The mafia heir seemed to pay no mind to his request. Instead, he leaned into him again, the grin returned to his face. "I know you have a lot of things that you want to know about me," he half whispered.

"Huh?"

"You answer my question; I'll answer your question too. How's that sound?"

Castiel only hesitated for a moment, before agreeing to him.

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><p>At first, Castiel disagreed when Dean told him to leave his car on the precinct's parking lot. He was only agreeing after the blond haired man had somehow convinced him that he would take him back to his car after they have drink. The detective only hesitated briefly when he followed the other man to his car, a sleek black car that seemed to match her owner's persona.<p>

Now, Castiel was regretting his stupidity for taking that offer so easily. He really wanted to leave the bar that Dean took him to, but then he would need to call a cab to go back to the precinct. To say that he was pissed off was understatement.

"You lied to me," Castiel hissed at the man who was sitting on the chair across from him, giving him the best glare he could make. The glass of beer in front of him was still untouched.

Dean just grinned widely. "No, I'm not," he replied nonchalantly.

"Yes, you are!"

"No, I'm not. Ask any question other than that, and I will answer it."

"You said you would answer all my questions."

"Yeah, I'll answer all your questions, as long as it's not about my family," Dean countered readily, the grin still plastered on his face.

Castiel scowled at him. "I should know better than to trust you."

There was a short moment of silence following his remark, before Dean broke it with a low chuckle. "Way to hurt a guy's feeling, Cas."

That words, whether Dean was serious or not, had somehow made Castiel feeling guilty, even if just a tiny bit. He decided not to counter that, though, turning his head away so the other man couldn't see his face.

Dean huffed. "Come on, just ask me something."

The detective finally relented. "Fine," he muttered, deciding that it was better than nothing. Sighing deeply, he thought of what he could possibly ask that wasn't related to the Winchester family. What crossed his mind was the question that had been directed at him just a while ago. "What's your favorite movies?"

Dean almost choked on his drink.

In the end, Castiel returned all Dean's questions back to him, and the blond haired man answered all the questions readily. His eyes glinted with mirth all the while, making the dark haired man wondered if the other man was finding this situation amusing.

Later that night, when Dean took him back to the precinct to take his car, the mafia prince asked him, "Are you free on Saturday night?"

Castiel shrugged. "I don't know yet."

"If you have time, I want to take you to dinner." Before the detective could open his mouth to reject it, Dean continued, "I will tell you about my family this time."

When Castiel asked why the sudden change, Dean just smiled at him and replied, "Because I want you to believe me."

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><p>Castiel finally decided that it was the perfect time to tell Gabriel about the Winchester matter, seeing as their caseload weren't too much at the time. He told his partner everything, from his secret investigation of the Winchester family up to Dean's dinner invitation on Saturday. Apparently it was a big mistake.<p>

The blond haired detective's reaction was downright unpleasant. He was raging, literally, spending almost twenty minutes scolding his younger partner for the recklessness and the unnecessary danger he put himself in, and then the next thirty minutes lecturing him about safety precaution of their job. Castiel got a nasty reminder of why his partner was considered one of the best detective of NYPD.

His dignity was hurt further when Gabriel practically dragged him to Chief Bobby Singer's office.

"Feather-brain, you never cease to amaze me," Chief Singer commented after the blond haired detective finished relaying the information that he just got from his younger partner. "You are a great detective, I know that. But even a great detective like you would only stand a small to zero chance once a mafia organization decide to hunt you down," he told the dark haired detective sternly. "You're lucky that Winchester guy seems to not having intention to harm you. _Yet_. I dunno, hopefully it isn't a temporary truce." The chief paused to take a deep breath, and then continued, still in stern tone, "If it was another mafia guy, I'm pretty sure you would already end up in a body bag."

Castiel bowed his head, feeling like a small child under the angry eyes of both Gabriel and the chief, even though he doubted their opinion about Dean. His latest encounter with the Winchester heir left him with an impression that the mafia prince wasn't a bad or a dangerous guy, save for his annoying attitudes. But he wouldn't say that in front of them. At least not now, when he didn't have proof to back up his statement. "I deeply apologize for my reckless act. And for making you worry."

Chief Singer's eyes softened upon hearing his apology. "Idjit," he muttered gruffly. "About your appointment with-"

"I'm not letting him go to a date with that mafia guy!" Gabriel suddenly bellowed, effectively cutting whatever the chief wanted to say and earning him an eye roll from the older man.

"For the fifth time, Gabriel, it isn't a date." Castiel glowered, blushing faintly. "It's just a dinner," he told them firmly.

Both Gabriel and Chief Singer stared at him with odd looks on their face.

"Yeah, yeah. Romantic dinner at Italian restaurant," the blond haired detective scoffed after a moment of silence.

Castiel rolled his eyes at Gabriel's remark before completely ignoring him, turned towards Chief Singer with a resolved look on his face. "Chief, please allow me to do this. This is the only way for me to get more information about the Winchester."

Knowing that there would be nothing he could do to make the stubborn detective change his mind, Chief Singer finally looked at Gabriel with a resigned look on his face. "You idjit. Go with him tomorrow night. Don't let him out of your sight."

_**To **__**B**__**e Continued**_

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><p>Thanks to all of you who have read my fic. Please tell me what you think about this chapter! Love this or hate this? XD<p>

Hints for the next chapter? Hmm, let's see. Undercover job and the appearance of another mafia lord? I kept getting new ideas when I wrote this chapter, so it seems that this fic would have at least two more chapters! XP

Once again, no promise of when I will update this fic. But one thing for sure: your review is what motivates me to keep writing!


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